Ethanol → 3-(Benzyloxy)-4-(2-methoxyethoxy)aniline

HRID 2274263Notes

Reaction equation

HRID 2274263 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:10]=1[O:18][CH2:19][CH2:20][O:21][CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.Cl[Sn]Cl.C(=O)(O)[O-].[Na+]>O.CCCCCC.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH:12]=[CH:11][C:10]=1[O:18][CH2:19][CH2:20][O:21][CH3:22])[NH2:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 867243352-(Benzyloxy)-1-(2-methoxyethoxy)-4-nitrobenzene

Product 1

HCID 867243363-(Benzyloxy)-4-(2-methoxyethoxy)anilineYield 33.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
80 °C

Procedure

In a 50 mL 3-neck RBF equipped with a magnetic stirrer, reflux condenser, and thermo pocket were charged 2-(benzyloxy)-1-(2-methoxyethoxy)-4-nitrobenzene (2.00 g), ethanol (15 mL) and SnCl2 (4.49 g). The reaction mixture was heated to 80° C. for 3 hr. The reaction was monitored by TLC using hexane:ethyl acetate (5:5) as mobile phase. After completion, the reaction mixture was allowed to cool at room temperature. The reaction mixture was poured in water and basified by using saturated sodium bicarbonate solution. Product was extracted with ethyl acetate (50 mL×3) and the organic layer was washed with 50 mL brine solution. Organic layer was dried over sodium sulfate and concentrated under reduced pressure. Crude material was purified by using Combiflash chromatography. Product was eluted with 30% ethyl acetate in hexane to give 0.600 g of 3-(benzyloxy)-4-(2-methoxyethoxy)aniline. 1H NMR: DMSO-d6 (400 MHz): 3.348 (s, 3H), 3.556-3.580 (t, 2H, J=4.8), 3.928-3.951 (t, 2H, J=4.4), 4.702 (s, 2H), 5.006 (s, 2H), 6.004-6.031 (dd, 1H, J=2.4, 6), 6.334-6.340 (d, 1H, J=2.4), 6.676-6.697 (d, 1H, J=8.4), 7.303-7.339 (m, 1H), 7.373-7.410 (m, 2H), 7.438-7.747 (m, 2H).

Workup

  1. customIn a 50 mL 3-neck RBF equipped with a magnetic stirrer
  2. temperaturereflux condenser
  3. temperatureto cool at room temperature
  4. extractionProduct was extracted with ethyl acetate (50 mL×3)
  5. washthe organic layer was washed with 50 mL brine solution
  6. dry with materialOrganic layer was dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customCrude material was purified
  9. washProduct was eluted with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-82bebb26163647f6a47e22a903c62f78
Source dataset
uspto-grants-2015_09
Patent number
US09126950B2

Reaction notes

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